


Always My Pretty Baby

by taiyou_nii_chan



Category: Supernatural
Genre: Blushing Sam Winchester, Bottom Sam, Bottom Sam Winchester, Chinese Dress, Dean Winchester Loves Sam Winchester, Dean Winchester and Sam Winchester in Love, Dean adores Sam, Dean likes Asian things, Established Dean Winchester/Sam Winchester, Feminization, Later Seasons Sam and Dean, M/M, MILF Sam Winchester, Mom Sam Winchester, PWP, Praise Kink, Sam is Dean's Wife, Sam is Female Coded, Self-Esteem Issues, Sibling Incest, Soft Sam Winchester, Top Dean Winchester/Bottom Sam Winchester, dean has a fetish, lots of sweet talking, mentions of weecest
Language: English
Status: Completed
Published: 2021-02-22
Updated: 2021-02-22
Packaged: 2021-03-12 03:55:47
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,816
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29628729
Author URL: https://archiveofourown.org/users/taiyou_nii_chan/pseuds/taiyou_nii_chan
Summary: Sam has always been Dean's "pretty baby" but years have gone by and he hasn't been feeling "pretty" or "a baby" lately. Dean takes care of fixing that.
Relationships: Dean Winchester/Sam Winchester
Comments: 13
Kudos: 73





	Always My Pretty Baby

**Author's Note:**

> This came up because I was re-watching later seasons where Sam is the ultimate MILF. Also, he deserves all the love and caring and feeling like the gorgeous thing he is, which is Dean's job, so that's where this came from. It has mentions of weecest during teenage years and crossdressing, so if you don't mind, please enjoy reading!

Sam remembers pretty well that he had started being intimate with his big brother since they were very young. It had been so natural. Since he had hit puberty, Dean knew he liked pretty things and Sam had been the prettiest thing he had ever laid eyes upon, right there, next to him all the time, with his sweet eyes, cute mouth and lovely dimples. As if he was a gift, just for him, and he would have to be an idiot to not take what he had been granted right into his arms. It had been the natural outcome for them. The incest thing hadn’t even been an issue except for having to be careful of not being found out, which actually had made everything hotter. Besides, Dean always had a naturally overactive sex drive, and Sam was a horny kid too.

And when he though back to the times before he left for Stanford, Sam could perfectly remember all the sexy things he used to do with his brother when they were young. He remembers very well how Dean made him feel pretty, how he kept telling him he was his baby, cute and adorable and so hot. He remembers Dean asking him to dress up in costumes, in uniforms, getting him pretty panties or lingerie and he remembers feeling sexy and pretty and wanted all the time.

It had taken a little bit of time when they got together again, but in the end things had come to be the same as before. After the first few tentative steps they took, testing the waters after being apart for two years, Sam was pleasantly surprised when he found out his brother still liked making him feel like a pretty baby, and he still enjoyed it as much as when he was younger, despite the time that had gone by and how much they both had changed through the years.

Lately, however, Sam hadn’t been feeling that. Years had gone by flying and after going through more than one apocalypse, Sam hadn’t even noticed when he had left his twenties behind and was now in the midst of his thirties, leaning towards his forties. He was now too far from his younger years. Gone was the soft, delicate body and high pitched voice. Now he could see the years on him when he looked at himself in the mirror and although he was proud of the person he had become, and of every scar and mark on his body, he couldn’t help but notice that things had changed. As it was natural of course.

Take Dean, for example. He had been astoundingly attractive in his younger times, but years had gone by and made him even more gorgeous, as if emphasizing his attractiveness. Like people used to say, he aged just like fine wine. The lines that appeared on his face when he laughed and smiled, the deep tone of his voice, everything made Sam think that this man couldn’t be real. It wasn’t fair, to be honest. Sam didn’t understand how could he keep feeling his heart skipping beats when he caught glimpses of Dean working on the guns, or cooking, or doing anything and the sunlight got caught on his darkened blond hair, on his long eyelashes and his scruff. How was it possible for Dean to still make Sam’s pulse get crazy when he leaned close to whisper something on his ear during a case, sending shivers down his spine, making him want to drown on his scent and his warmth? It was a mystery to him how he could still make Sam feel weak in the knees when he looked straight at him, at his eyes, and smiled, that confident playful grin that should be illegal, with the tip of his tongue pressed under his white teeth and light reflecting on his beautiful green irises.

So, Sam was okay with change, it had done wonders on Dean and it was just part of the natural flow of time, it was proof of the road they had gone through. And although he had noticed he didn’t look like what Dean used to call “my pretty baby” anymore, he hadn’t really been thinking about it until lately.

These days they had been so busy and tired they hadn’t had a lot of time to be intimate, not like before at least. Not like those younger days when they took entire days or nights to dedicate just to each other. On top of that, learning to take care of Jack had been using most of Sam’s free time. He loved the kid and he was determined to help him feel good with who he was, he would never let someone go through the same stuff he had, so Sam had even started doing research on it. And before he noticed, he was already spending a lot of time reading books about good parenting.

He had finished a couple of them through the nights, ¬—despite Dean’s complaints about them both being tired and the light from the lamps being annoying— and quickly tried to get new information.

He had been looking for new ones at a library, during a break from a hunt, when he bumped into a lady about his age, holding a toddler’s hand. He apologized and she smiled at him, noticing the title of the book he was holding.

“If it’s about raising gifted kids, I suggest this one.” She said, picking another book from the shelves. “The author is known for making things easier to understand and more practical.” She said, offering a different tittle. Sam looked at the contents and was immediately interested. She grabbed another one. “This one is good too, but it’s more oriented to be read by both parents. I tried reading it with my husband but it was a complete failure, that man thinks we’ll figure everything out on the road.” She laughed and Sam couldn’t help laughing with her, immediately picturing Dean.

“Yeah, I know how that goes. My… partner is the same.” He smiled and she joked about feeling relieved she was not the only one dealing with that kind of person. After a few more comments that Sam understood perfectly, he finally thanked the lady and spoke with her close to 10 minutes about some other books she recommended, among other parenting issues, until she left.

Sam had never felt more like a mom before.

It wasn’t a bad feeling of course, it was just new. And different. Like all of those things that had changed throughout the years. But the moment he noticed them, he couldn’t stop himself from thinking about them a little more. Still, it wasn’t like it was bothering him, no.

At least not until a certain night he had finally taken a break from everything else to dedicate time to himself and Dean, he had even asked Castiel to take Jack out for the night, which his big brother had very much appreciated. Dean had offered drinking while watching a movie together and Sam had agreed, already thinking about how he would smoothly set the mood to take Dean’s attention from the movie towards himself and maybe finally spending the night awake and sweaty, instead of tired and asleep.

And everything was going fine until Sam started getting annoyed at Dean for being so oblivious at his intentions, paying too much attention to the movie. It was then that it actually bothered Sam.

They were watching a movie in which Dean couldn’t stop praising the young girl on the screen, being all sexy and sweet with her older lover. The actress was gorgeous, a pretty lady who actually looked about 10 years younger, and part of the movie was about the forbidden love of this young girl and an older man. She was still at college and she could come home and dress pretty for him and didn’t have a kid to take care of, and Sam was suddenly feeling very upset. He wasn’t like that anymore, they hadn’t had time for themselves in a while and Dean wouldn’t shut up about what the girl was doing, suggesting Sam should take her example, and Sam couldn’t take it anymore.

“You know what Dean? If you like that type so much, maybe you should go get some college girl to drink and watch a movie with you, instead of putting up with me doing research or reading books the whole night, keeping you up with the lamplight, right?” Sam snapped, unable to control himself, and he stood up, leaving the room, not having to look back to know his brother had stayed on the couch, dumbfounded.

He hadn’t mean to sound like such a jealous wife throwing a tantrum, he truly hadn’t, and he immediately felt really embarrassed the moment he was alone in his room. He sat on his bed, covering his face with his hands, and sighed deeply. He hadn’t mean to screw up his night with Dean. Maybe he should go back and apologize to Dean for snapping at him when he wasn’t at fault for anything. The last thing he wanted was to mess up the night they were finally spending time together.

“Sammy?”

Dean’s voice startled Sam and he looked up from his hands, finding his brother standing at his still open door. He hadn’t even closed it when he came inside, too busy regretting his sudden sour mood. He couldn’t stop the warm feeling of embarrassment on his face and he sighed, but before he could say anything, Dean came into the room.

“What’s wrong?” He asked and Sam noticed he was kind of concerned. Of course, it was normal for Dean to tease him like what he had been doing while watching the movie, he could usually put up with it, with much more, to be honest, and he never let it get to him. It was mandatory for Dean to tease his baby brother at any opportunity he had. So Sam understood his brother’s worry, he would never react like that over some innocent, silly teasing. He sighed again and tried to reassure his big brother.

“I’m sorry, Dean. There’s been a lot of stuff in my head lately and I guess it just came out all at once. Forget it, please. Let’s go back, I wanna finish the movie with you.”

“Don’t be stupid Sam, I don’t care about the movie. I wanna know if you’re okay. What’s wrong? What’s this you’ve been thinking about and why haven’t you tell me?” Dean asked, crossing his arms over his chest, frowning at his little brother.

Sam sighed deeply. He should have known Dean wouldn’t drop the subject that easily.

“Nothing, Dean, it’s nothing. I don’t wanna ruin our free night with this, I want us to enjoy it.”

“Yeah, well, I’m not going to enjoy shit while you keep everything to yourself, letting it eat you from inside, alone. C’mon, tell me what’s happening. And stop sighing like that, c’mon.” He said, gesturing to Sam with his hand, asking for him to start talking.

“It’s just… it’s a stupid thing…” Sam tried again, still doubtful about speaking about the things that had been moving around on his head.

“I love stupid.” Dean said, nonchalantly, and Sam snorted, relaxing a little. He looked at Dean for a moment and decided it wouldn’t be bad to be sincere, that was what they always needed.

“It’s just…” Sam rubbed his hands together, nervously. “I’m sorry.” He finally said. Dean frowned.

“For what?”

“I was just… remembering how things were a little different… I mean, like, when we were younger. You know, like… the movie we were watching…” Sam glanced shyly towards Dean and he noticed his brother’s confused expression cleared up. He understood immediately and smiled playfully, probably thinking back at his fond memories, but before he could comment anything, Sam continued. “And when I saw that girl and you liking the things she did… well… I know I’m not ‘pretty’ or ‘a baby’ anymore, so this is all very stupid, but I couldn’t help feeling jealous and-…”

“Wait, wait, what? What was that? What the hell did you just say, Sam?” Dean interrupted him, frowning, shocked. Sam tried to stay relaxed; he was mature enough to have this conversation right? Still, his cheeks grew hot and he knew they were red now, making him feel a little bit more self-conscious.

“Don’t make me say it again, Dean. It’s already embarrassing enough.” Sam closed his eyes and sighed. “I’m trying to say I understand if you’re disappointed or tired of me. And I really want to change that, so…”

“Sam.” Dean interrupted him. “Are you trying to say…? Did you just…?” Judging from his expression and his voice, Dean seemed to be feeling a mix of amusement, disbelief and indignation. “You think I don’t find you attractive anymore or something like that?”

“I… I mean…” Sam stuttered, something unusual on him, and his face grew warmer, which Dean could perfectly see. “I’d understand.” Sam swallowed. “I’ve changed. Hell, we’ve both changed and… yeah, I’m not like… you know, like I was years ago… not like… like the girl in the movie… and I’m not excusing myself, I didn’t mean to make a scene either, I’m just…”

Dean’s snort interrupted Sam and he looked at his big brother, confused and a little offended. Dean was snickering and sighing, taking a few steps closer to where Sam was sitting on his bed.

“Man, I really wonder how you can be so smart and so stupid at the same time.”

“Excuse me?” Sam’s eyes opened big and his eyebrows rose up, making Dean snicker again.

“So that’s what’s been going on lately. I knew I had seen you ‘brooding and pensive’ these days.” Dean teased him, grinning, and sat down next to him, on the bed. “I know when you’re making sad-Sam or worried-Sam faces, you know?”

“I’m not-…” Sam blushed and frowned, a little hurt that his brother was taking it as a joke. “Dean, I was being serious here but if you’re gonna make fun of me, I’m not gonna-…”

“Shh, no no, come here.” Dean said, grabbing Sam by the shoulders, stopping him from getting up and leaving, and then holding his face with his hands. He was still smiling, a little amused, but his voice grew softer and sweeter. “I’m not making fun of you, you silly Sasquatch.”

“Dean, let go of me, I’m not-…” Sam tried to move away, feeling more embarrassed, but Dean stopped him again.

“C’mon, _baby._ ” Dean whispered, sweetly, softly, right next Sam’s ear, making him shiver. “It’s okay.”

“D-Don’t call me that, Dean-…”

“Why not? You’re _my sweet baby.”_

Sam felt his pulse jumping up and familiar tingling things all over his body. Well, something that definitely hadn’t changed with the years was his reaction to those words.

“S-Stop, you’re just…” Sam swallowed. “Just because I said all of that you don’t have to-…”

“Oh Sam, you’re such an idiot, baby.” Dean said, but this time his voice wasn’t amused. It was endeared, as if he was looking at the most adorable thing in the world. “Do you really think I don’t find you attractive anymore? That I don’t see you as my pretty baby, like before? Like always?” Dean kissed him on the lips, soft and delicate, as if it was the first time, when Sam was 13 and Dean was trying not to scare him with it, to show him how kissing went. Sam closed his eyes and Dean groaned, pleased, delighted, making Sam feel butterflies on his stomach. “Silly baby boy, how can you think that?” He mumbled, still kissing him. “But… It’s probably my fault, right? I guess I haven’t been showing my sweetheart how much he still makes me crazy, how he always has and always will…” He mumbled over Sam’s mouth, nipping at his bottom lip, their breathings getting rougher. He sucked on it, humming and Sam moaned. “I’ll make up for it.”

“N-no, Dean, it’s not your… I’m the one that…” Sam tried to say something but he wasn’t being very eloquent, Dean’s familiar sweet words were making a mess of him, he felt hot and weak and wobbly and he still liked it so much he couldn’t help feeling embarrassed at himself.

“Shh, easy, honey.” Dean whispered, licking at Sam’s mouth and sweetly caressing Sam’s face with his big, rough hands. “Silly Sammy.” Dean sighed. “You’re still the sweetest thing I’ve seen in my life. My pretty Sammy, my baby brother.” Dean said, biting Sam’s lip and tracing his thumbs on Sam’s face, which Sam knew wasn’t as smooth and delicate as before, but his brother was touching him with the usual adoration and he couldn’t help shivering and sighing.

“Dean…” He moaned, feeling again like the horny teenager on a motel room that couldn’t wait until their dad left to have his big brother, to give himself to whatever he wanted to do to him. How had Dean done that? How did his brother always manage to make him _feel_ so much?

Dean kissed him deep, slow, sensual, bringing their bodies together to grind against each other, touching and caressing, turning them both into a hot, wet, panting mess in just a moment. Sam shivered when Dean’s hand tangled itself on his hair and pulled, groaning wantonly.

“Oh, Sammy, how could you _ever_ think I wouldn’t want you, sweetheart? That I wouldn’t want this?” He growled, pulling Sam’s head a little back, to look at his face and his body. Sam whined when he saw the way Dean was staring down at him, hungry, lustful, making him feel so wanted, making him get immediately hard. Dean kissed him once more before leaning back again, pulling on his bottom lip with his teeth, looking him up and down for a second time. “You make me crazy with just the way you breathe, baby, for fuck’s sake.” He groaned and Sam whimpered, his whole body trembling.

“Are you… really…?” Sam mumbled clumsily and Dean broke the kiss to look at him. And when he looked at Sam there he was, still the same, still that precious baby, with his doe hazel eyes , looking at him doubtfully from under his pretty eyelashes, blushing and panting, pupils blown with lust and want but brows furrowed in silent hesitation. It didn’t matter if time had now left its traces on Sam’s body and face, Sam was a work of art, he was life’s masterpiece. And still, he clumsily bit his bottom lip and Dean growled, pushing Sam down into the bed and immediately getting on top, tracing his mouth over Sam’s jaw, enjoying the slightly rough feeling of his stubble, and then bringing his mouth down to Sam’s strong beautiful neck, kissing, licking and biting.

“Sammy, haven’t you seen how people look at you?” Dean groaned, pressing his body against his baby brother’s bigger one and immediately grinding down against it, humping him shamelessly, unable to resist how Sam made him go feral and senseless, like an animal in heat. “Haven’t you noticed how there are always turning heads wherever you walk into?” He whispered, heatedly, and looked at Sam panting under him, a confused and disbelieving look crossing his face. Dean growled again, lifting Sam’s shirt up to his neck. “God you’re so cute.” He groaned and brought his mouth down to suck on Sam’s already hardened left nipple. Sam writhed and moaned, his back arching up, pushing his chest up against Dean’s face, chasing the feeling of Dean’s mouth and tongue. “Whenever I see them wanting you it makes me so fucking jealous, but at the same time I want to show you off, to let everyone see how hot you are and how lucky I am, it all makes me crazy.” Dean mumbled on Sam’s nipple and looked up at him. “You make me crazy, baby.”

“Dean” Sam pleaded, his eyes watery, his face red and sweaty, too much feelings tearing him apart, he didn’t even know what else to say except for his big brother’s name. “Dean.” He moaned again, while Dean sucked now on his other nipple, his hands holding him in place so he could rub against him while Sam’s hands went up Dean’s back, and behind his head, tracing his nails on Dean’s favorite places, making him growl. They knew each other too well, every little spot, every detail that turned them on, that made them feel good, but somehow every time it was as exciting as the first time, to make each other grow wild and desperate with want.

Dean went up to Sam’s face to kiss him again, wet, heated and sensual, tongues caressing inside mouths, pants filling the silence in the room along with the creaking noises of the bed when they rubbed against each other. It was a symphony they knew since they were young, but with slightly deeper voices instead of the high pitched ones from those times. It was as if the melody was now ripe, perfected, honed and polished to be played without doubt or hesitation.

They somehow managed to get rid of each other’s clothes, Sam pulling Dean’s shirt up his head desperately, and then taking off his own while Dean unbuckled his own belt, stopping when he saw Sam working on his own jeans, taking them off with a little effort, since they were still tangled on each other.

When Sam was finally free of all his clothes, he finally noticed Dean was staring down at him intently. He looked dazed and his eyes roamed up and down his baby brother’s body. Sam felt his heart pumping so hard and fast on his chest he thought it was going to explode. And then, Dean bit on his bottom lip, dragging his teeth slowly on it, that incredibly sexual gesture Dean did when he was impossibly turned on.

 _“Holy crap.”_ Dean growled, panting. “Look at this _babe.”_ He moaned, and Sam felt he could cum just from those words and the way Dean was looking at him. He moaned helplessly, leaking precum, and Dean went down on him to lick it and suck the tip of his cock, but Sam knew he wouldn’t last if he did that, so he whimpered, shaking his head and pushing on Dean’s shoulders.

“No, no, Dean, inside me, get inside me now, please.” He begged desperately, grabbing his legs to bend them against his chest, keeping them open and offering himself to Dean, showing him he had gotten himself ready way beforehand. “I can’t anymore, I need you inside me.”

Dean looked at Sam’s pink hole, twitching, lubbed and pretty and ready for him, and he made a sound that was both a moan and a growl, lustful and desperate. He pushed his fingers inside him, testing how soft he was and Sam whimpered almost painfully desperate, unable to stop his hips from pushing down against them.

“Look at this sweet pink little thing…” Dean moaned. “That’s my pretty Sammy, always ready to take big brother inside you, right, sweetheart?” Dean panted. “My good baby boy, my cute little Sammy.” Dean praised him, taking his fingers out and kissing his mouth while stroking himself before going inside, and Sam swooned, whimpering. “You’re so perfect for me, baby brother, my pretty bitch.”

“C’mon Dee, please, stop being a jerk…” Sam wailed. “I can’t anymore, please.”

“Shh, shh, okay baby, it’s okay.” Dean cooed at his brother in the same sweet way he did when he was little, the same way he always did because to Dean’s eyes, Sam would always be his baby. “I’ll always give you everything you need.” He kissed him on the mouth and finally, _finally_ he grabbed his cock to place himself against Sam’s hole and push inside, making them both groan and sigh. Their bodies immediately recognized each other, adjusting perfectly, as always, exquisite waves of pleasure running over them, and Dean replaced Sam’s hands under his knees, now being him who was holding his legs open and bent, his body pinned against the bed under him.

Dean didn’t lose time, he couldn’t wait at all and once he was fully inside, he immediately went for a frenzied rhythm, roughly trusting his hips in and out of Sam, relishing on tightness around his dick, and making Sam’s ragged pants turn into whimpers and his arms try to hold onto his big brother’s shoulders. Dean was panting and moaning too, unable to hold himself back. Sam had no idea the rush of delight and pride that it gave Dean to look at him when they did this, knowing how he could subdue Sam’s huge and strong body, keeping him pinned to the bed, pleasing him, taking him apart, fucking him into the mattress, making him melt and twist and cry, helpless and pliant. For Dean, knowing he could always turn his now mature, strong and ever-composed brother into this exquisite mess made blood pump almost painfully in his heart and push him relentlessly to the edge.

“Dean, Dean…’s too good, so good, I can’t, I can’t-…” Sam whined, wet eyes closed and furrowed brows. He could barely breathe and each one of Dean’s thrust hitting the right spot, throbbing inside him had him immediately gone, it was too good, he wasn’t going to last anymore. “I wanna… I’m… Dee!”

“It’s okay, it’s okay sweetheart.” Dean panted, moaning at feeling Sam exquisite tightness around him and he kept mercilessly thrusting into Sam’s sweet spot. “It’s okay, baby, let go, cum for big brother, Sammy, c’mon.” Dean panted against his mouth and Sam’s body writhed and twisted and he finally burst into a million stars, his back arching and his mouth opening to let out lovely whimpers and whines while milky spurts of cum came out of him. Dean praised him through it, telling him how pretty and perfect he was, making it even sweeter for Sam.

He kissed Sam sweetly, slowing a little but without stopping, holding him down to keep pushing into him until Sam’s wobbly hands grabbed behind Dean’s waist, pushing him against him and Dean growled, speeding up again. He looked down at Sam, absolutely wrecked and messy, shaken and panting with every one of his pushes into him, and he couldn’t believe this beautiful thing really belonged to him. He felt his thrusts getting desperate and erratic, loosing rhythm when the blood was pumping on his veins as if he was going to explode. And when one of his baby brother’s hand went up to the back of his neck to pull him towards his mouth to kiss him, still dazed and trembling, and whispered “Want your cum inside me Dean, please?” in the sexiest voice ever, as sweet as the first time those obscene words had left his mouth, Dean closed his eyes and came hard and so good, groaning while filling Sam up with his cum, stuttering hips finally coming to a stop before his whole body collapsed on top of Sam’s.

When he felt his breathing had calmed down, Dean rose up to look at his baby brother and grinned, his chest swelling, proud of the state he had left him on. Sam looked so perfect like that, happy and sated, and fucked _so good._ One of his hands went to Sam’s face to brush his wet hair out of it, and then Sam looked at him, still a little dazed. After a few moments, he smiled, his adorable dimples showing, making Dean feel warm and soft.

“Hey.” Dean finally said, after a long, nice moment of silence, and playfully slapped Sam in the head. “Don’t ever let those stupid ideas into your head again, ‘kay, kiddo?”

“I’m sorry.” Sam said, rushing to apologize as usual and Dean rolled his eyes, endeared. “I guess I’ve been so busy lately, with Jack and everything else and… I don’t know I guess… I couldn’t help overthinking everything.”

“Yeah, you always do that.” Dean frowned. “I hope next time you tell me about it before it comes out like this, I was honestly worried for a moment. I didn’t think a little bit of teasing would make you so upset, you know? I thought I had screwed something up… again.”

“Don’t say that.” Sam smiled. “I was just… you know, looking at the girl and you kept going on about her dressing pretty and doing things and I guess I was…” Sam’s voice grew lower. “Jealous. Especially since it’s been a while since I haven’t… you know…” Sam looked away, a little embarrassed. Dean smiled, completely charmed.

“What? Dressed pretty for me? Done sexy things for me?” Dean asked and Sam bit his bottom lip. “Yeah, I’ve been missing it too.” Dean caressed Sam’s wet hair with his fingers. “But we’ve both been working so much lately, and you’re doing a lot for the kid. I’ve seen how tired you end up, always taking care of a lot of stuff, of everyone else before you. The last thing I wanted was to add stress to that, asking you for more.”

“You mean…” Sam’s eyes opened wide, looking at his big brother. “You would… still… want me to…?”

“Are you stupid Sam? You’re speaking as if I’ve ever NOT wanted you to.” Dean seemed a little annoyed, still shocked at Sam’s ridiculous doubts. If his little brother knew how everyone around him thought of him he might finally grow confident on himself.

“But I… I’m not…” Sam mumbled, but Dean looked at him as if he was going to slap him if he dared say something along the lines of not being Dean’s pretty baby anymore, so he didn’t finish. He blushed when the realization hit him and then Dean smiled, wide and playful.

“Actually… This might be a good time to finally show you something I got for you a few weeks ago.”

Sam didn’t even know what to comment when he saw the beautiful Chinese-styled sexy dress Dean was showing him with a huge, flirty, dorky smirk plastered on his face. The color was blue overall, with beautiful golden and soft green patterns and details, lacey decorations and a very provocative outline. It looked like something that came out of one of those erotic videogames Dean played sometimes, where the girls wore sexy clothes as if it was the most common thing. At first Sam wanted to ask Dean what was it with his Asian oriented fetishes, but instead he voiced out the first thing he thought when he saw the lovely piece.

“Dean, I’m not gonna look good on that.” Sam said, snorting as if it was the most obvious thing ever.

“C’mon, you haven’t even tried it yet. Try it.” Dean insisted, as it usually took some convincing to have Sam wearing something new.

“I don’t have to, I already know. I’m sure it’s not even my size.”

“Oh, it is, don’t think I didn’t make sure of that first.” Dean smiled, proud of himself. “C’mon, just try it. Just once.”

Sam would have insisted on being sure something so extravagant and overall feminine wouldn’t ever look good on him, but wasn’t he the one suffering before for not being proactive towards Dean’s needs lately? It would be ridiculous if he kept refusing. So, even when he felt it would be a disappointment, he complied to his brother’s wishes.

It was a little difficult to get dressed by himself, but he didn’t want Dean to see him before he had it completely on, so when he finally told his brother he could come into the room again, he couldn’t help feeling a little self-conscious, scared of disappointing.

“Just don’t laugh, okay?” Sam mumbled, avoiding Dean’s face. However, his brother didn’t answer back and he had been so busy feeling embarrassed he hadn’t noticed Dean had gone quiet the moment he came back into the room. When he finally looked at him, he noticed the way Dean was staring at him, eating him up with his eyes. “D-Dean?”

“Oh, Sammy.” Dean growled, half-lidded, lustful eyes. “Not even close.”

“What?”

“My fantasies. They're not even close, you’re too gorgeous, baby.” He mumbled, immediately coming closer, unable to stop himself. Sam felt his heart jumping on his chest. “It’s not fair. You can’t be real.”

Sam felt his whole face growing warm and his body reacting immediately. Dean came closer but he seemed hesitant, as if he didn’t want to break the illusion by touching him.

“Y-You like it?” Sam mumbled in a low voice, following Dean’s beautiful green eyes while they moved all over Sam’s body, appreciating the way the dress highlighted his figure, his narrow waist and pretty long legs, matching his eyes and pale skin. Dean bit on his lower lip while humming approvingly.

“Fuck, it even flatters your boobs.” He said, while looking at the overture in the shape of a diamond over Sam’s chest, showing his pretty skin and curves, and Sam felt the urge to bitch-face his brother, but he was too embarrassed and getting too aroused to get completely angry.

“Dean.” He said, trying to sound annoyed or warningly, but it came out softer and Dean snickered.

“What? I love them. You’ll be a wonderful mom, you know?” Dean teased him, grinning playfully again and Sam was going to say something, but Dean’s hands finally coming to hold his waist interrupted him. “Yeah, my baby’s grown, but you’re still my pretty baby. Always my baby.” Dean moaned and Sam stuttered, blushing. “You always blush so pretty and cute, sweetheart.” Dean mumbled and leaned into Sam’s face to kiss him on the lips. Sam kissed him back, sighing. Dean’s hand went down to caress Sam’s legs with ease, thanks to the dress and Sam gasped, throwing his head back, showing his long and pretty neck. “God, you’re so sexy.” Dean growled, breathless. “Gorgeous.”

“Dean.” Sam sighed, delighted, gleeful. He really didn’t think he could be so fortunate, that things could still be the same between them, even now. He felt like crying. “Dean.” He moaned again. Dean licked at his neck and then he went up to his ear, sucking his earlobe.

“Did you put on the panties too, sweetheart?” He whispered, hot and hungry, licking at Sam’s ear. Sam shivered and panted. He bit his bottom lip and leaned back to look at his big brother.

“Why don’t you find out by yourself?” Sam purred, smiling, feeling again like that playful kid from a long time ago that dared to wear a skirt for the first time. The exquisite sound Dean made had Sam feeling weak on the knees, so turned on and feeling so sexy.

“That’s my Sammy.”

**Author's Note:**

> Thank you so much for reading! I hope you enjoyed reading it as much as I enjoyed it writing it. If you did, it'd be wonderful if you let me know whatever you'd like to comment about it, it truly gives me life!


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